The Best Cycling Routes in Siena - Tuscany
Discover the best cycling routes in Siena - Tuscany, Italy. Our curated collection includes 13 handpicked routes, from shorter coffee rides to challenging all-day rides. The region offers hilly terrain, ideal for riders who enjoy rolling landscapes and varied terrain. Each route includes GPX files, detailed elevation profiles, highlighted climbs, and recommended cafés stops along the way.
13 routes
The beauty of Rapolano Terme
Rapolano Terme, the finish of stage six of the 2024 Giro d’Italia, is an ideal base for exploring this part of Tuscany. This route reaches Sinalunga, on the border with the province of Arezzo. The toughest climb follows the Lauretana road, scenic and quiet. Asciano and Serre di Rapolano are the final villages where you can experience a typical day in the Siena area.
San Gimignano, Volterra & Monteriggioni
A feast of Tuscan hills. The route passes some of the most iconic villages in the provinces of Siena and Pisa, including San Gimignano and Volterra. The climb to Volterra, about 8 kilometers at an average of 5%, is a perfect excuse for a proper Tuscan lunch.
Eroica loop from Gaiole in Chianti
Gaiole in Chianti is well known in the cycling world as the home of the Eroica. It is a historic reenactment of early cycling: for one day, thousands of riders use vintage bikes, wear 1920s-style clothing, and ride the dusty white roads. This route follows the opening and closing sections of the permanent Eroica course. The climb to Brolio Castle is especially beautiful.
Pienza & the best of Val d'Orcia
This ride through the Crete Senesi begins and ends in Montepulciano, known for one of Italy’s finest red wines. The first climb of the day leads to Pienza, whose historic center is a UNESCO World Heritage site. Through a beautiful sequence of hills, you return to Montepulciano via Bagno Vignoni, San Quirico d’Orcia, and Chianciano Terme.
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Plan Your Visit to Siena - Tuscany
Discover where to stay, climbs, routes, bike rentals, cafes, and everything you need to plan your cycling trip in the Siena - Tuscany Guide.